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247065

Sigma-Aldrich

(S)-cis-Verbenol

95%

Synonym(s):

(1S,2S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-ol

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
18881-04-4
Molecular Weight:
152.23
Beilstein:
2206582
EC Number:
235-908-8
MDL number:
MFCD00065444
UNSPSC Code:
12352000
PubChem Substance ID:
24854847
NACRES:
NA.22

Quality Level

200

Assay

95%

form

solid

optical activity

[α]20/D −9° in chloroform
[α]20/D +10° in ethanol

optical purity

ee: ≥50% (GLC)

mp

62-65 °C (lit.)

functional group

hydroxyl

SMILES string

CC1=C[C@H](O)[C@H]2C[C@@H]1C2(C)C

InChI

1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9-/m0/s1

InChI key

WONIGEXYPVIKFS-YIZRAAEISA-N

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General description

(S)-cis-verbenol is an aggregation pheromone component in the bark beetles. It shows potent anti-oxidative and anti-inflammatory activities.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBP0449
SHBN7440
SHBM7964
SHBM6059
SHBH6778

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Marica Lindmark-Henriksson et al.
Journal of natural products, 66(3), 337-343 (2003-03-29)
alpha-Pinene, both as the pure enantiomers and as the racemate, was transformed mainly to trans-verbenol by treatment with a Picea abies suspension cell culture. These reactions were followed by a slow transformation of the verbenol to verbenone, which was not
Kairomone response in Thanasimus predators to pheromone components of Ips typographus.
Bakke A and Kvamme T.
Journal of Chemical Ecology, 7(2), 305-312 (1981)
B Wang et al.
Bulletin of entomological research, 102(1), 71-77 (2011-07-23)
Interactions between invasive insects and their fungal associates have important effects on the behavior, reproductive success, population dynamics and evolution of the organisms involved. The red turpentine beetle (RTB), Dendroctonus valens LeConte (Coleoptera: Scolytinae), an invasive forest pest in China
P J Rice et al.
Journal of economic entomology, 87(5), 1172-1179 (1994-10-01)
House flies, Musca domestica (L.), and their eggs were treated with 22 monoterpenoids to determine the topical, fumigant, and ovicidal activity of each compound. Fumigant activity of 14 monoterpenoids were examined further using red flour beetles, Tribolium castaneum (Herbst). Third-instar
J O Levin et al.
International archives of occupational and environmental health, 63(8), 571-573 (1992-01-01)
The renal elimination of verbenols after experimental exposure to (+) and (-)alpha-pinene was studied in humans following exposure to 10, 225, and 450 mg.m-3 terpene in an exposure chamber. The pulmonary uptake was about 60%. About 8% was eliminated unchanged
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